I’m Jesse Wesson, an engineering leader based in Vancouver, BC with over twenty years of experience building software at companies like Microsoft and Apple. My career spans native application development, large-scale web infrastructure, CI/CD systems, and distributed cloud services — as well as leading the diverse, high-performing teams that build them.
I graduated from the University of Victoria with a B.Sc. in Computer Science with a Software Engineering specialization, and was awarded Apple’s WWDC Scholarship four consecutive years (1999–2002) — an early signal of where my career was headed.
I spent over a decade at Microsoft across several teams. I started in the Macintosh Business Unit working on Office for Mac test infrastructure, then moved to porting Word to the iPad and updating the ribbon for macOS. At BigPark I led development of the NFL on Xbox — including the first-ever live Super Bowl stream — and worked on HoloLens experiences and augmented reality systems. At MS News I managed a team of 10+ engineers responsible for article, video, and slideshow pages across desktop and mobile web. At WebXT I led the Engineering Systems team, building the build, test, and deployment infrastructure that supported tens of millions of daily active users across services peaking at over a million requests per second.
In 2022 I joined Apple in Vancouver, where I led a team contributing to Xcode Cloud — the CI/CD system used by Apple’s over one million registered developers — alongside internal CI infrastructure and bespoke tooling that accelerated Apple’s OS development.
Since mid-2025 I’ve been an independent developer, building Cocktail Concierge — a native iOS app in the Food & Drink category that tackles a deceptively complex problem: semantic ingredient search. I hold two US patents from my time at Microsoft, and I’m always looking for the next hard problem worth solving.
Skills
Languages
Swift · Objective-C · C# · Java · C · Shell Scripting
Platforms & Tools
iOS / SwiftUI · SwiftData · Xcode · Xcode Cloud · macOS · Azure · CI/CD
Strengths
Engineering Leadership · Distributed Systems · Microservices · Developer Tooling · Team Building · Agile · Data-Driven
Work History
Independent Software Developer
Jul 2025 – Present · Personal Start-Up · Vancouver, BC
Developing a universal Apple platforms application in the Food & Drink category, leveraging open-source projects and AI development tools to accelerate engineering efforts.
Senior Software Engineering Manager
Jul 2022 – Jun 2025 · Apple — Developer Tools · Vancouver, BC
Led a team contributing to Xcode Cloud, Apple’s CI/CD system for over a million registered developers. Also responsible for internal CI infrastructure and bespoke tooling that accelerated Apple OS development. Delivered an Apple Developer Tech Talk and supported developers in online forums and in-person sessions.
Principal Software Engineering Manager
Sep 2020 – Jun 2022 · Microsoft — WebXT · Vancouver, BC
Led the Engineering Systems team, providing build, test, and infrastructure for hundreds of engineers in a mono-repo producing thousands of builds per month. Services supported tens of millions of daily active users at peaks of over a million RPS. Transitioned the org from manual weekly deployments to fully automated CI/CD pipelines.
Senior Software Engineering Lead
Aug 2017 – Aug 2020 · Microsoft — MS News · Vancouver, BC
Engineering lead managing 10+ developers including an offshore team. Responsible for article, slideshow, and video pages across desktop and mobile web. Led multiple technology and UX migrations using experimentation to validate business impact and drive engagement.
Senior Software Engineering Lead
Sep 2015 – Jul 2017 · Microsoft — BigPark · Vancouver, BC
Led development of NFL on Xbox for 2015, including the first-ever live Super Bowl stream — achieving a record number of concurrent users. Developed HoloLens experiences and created a distributed system for tuning augmented reality algorithms using Azure and ML.
Senior Software Development Engineer
May 2014 – Aug 2015 · Microsoft — BigPark · Vancouver, BC
Tech lead on the NFL 2014 and 2015 app for Xbox One and Windows 8. Led development of the NextGenStats 2015 feature, marketed in a national TV ad campaign. Contributed to US Patent 10142697: Enhanced Interactive Television Experiences.
Senior Software Development Engineer
Feb 2013 – Apr 2014 · Microsoft — APEX · Vancouver, BC
Engineer on the Word for Mac and iPad team. Worked on porting the first version of Word for iPad, and implemented updated ribbon functionality for Word on macOS.
Senior Software Development Engineer
Jun 2010 – Jan 2013 · Microsoft — APEX · Vancouver, BC
Engineer on the automation infrastructure team. Designed and implemented Mac and iOS test harnesses to unify interfaces and replace multiple legacy systems. Contributed to US Patent 9588874: Remote Device Automation Using a Device Services Bridge.
Software Development Lead
Dec 2007 – Jun 2010 · Microsoft — MacBU · Redmond, WA
Grew a newly formed build team from two to six engineers. Designed a new build system supporting various product pipelines, led the team from design through delivery, and owned sustained engineering of multiple legacy products.
Software Development Engineer
Apr 2006 – Nov 2007 · Microsoft — MacBU · Redmond, WA
Owned Mac client components of the Office for Macintosh automation system. Created a distributed file fuzzing system that iterated through hundreds of thousands of files across hundreds of clients.
Software Development Engineer in Test
Mar 2004 – Mar 2006 · Microsoft — MacBU · Redmond, WA
Owned testing of several areas of Office for Macintosh including the AutoUpdate mechanism. Designed and coded a tool to test accessibility in Office for Mac.
B.Sc. Computer Science
1998 – 2003 · University of Victoria · Victoria, BC
Software Engineering specialization. Apple WWDC Student Scholarship recipient four consecutive years: 1999, 2000, 2001, and 2002.